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【结 构 式】 
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【分子编号】42053 【品名】tert-butyl (1R)-1-([[(1S,2R,18R,19R,22S,25R,28R,40S)-5-chloro-22-(cyanomethyl)-2,18-dihydroxy-32,35,37,50-tetramethoxy-40-[[(2-methoxyethoxy)methoxy]methyl]-15-nitro-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6). 【CA登记号】 |
【 分 子 式 】C66H76ClN9O21 【 分 子 量 】1366.8302 【元素组成】C 58% H 5.6% Cl 2.59% N 9.22% O 24.58% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The cyclization of (XII) by means of CsF in DMSO gives the tris macrocyclic compound (XIII), which is reduced at the NO2 group with H2 over Pd/C, yielding the amino derivative (XIV). The diazotation of (XIV) with t-Bu-ONO and HBF4, followed by reaction with CuCl2/CuCl, affords the corresponding chloro derivative (XV), which is silylated with Tbdms-N(Me)-COCF3 to provide the bis silyl ether (XVI).
| 【1】 Boger, D.L.; et al.; Diasteroselective total synthesis of the vancomycin aglycon with ordered atropisomer equilibrations. J Am Chem Soc 1999, 121, 13, 3226. |
| 【2】 Boger, D.L.; et al.; Total synthesis of the vancomycin aglycon. J Am Chem Soc 1999, 121, 43, 10004. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 42052 | tert-butyl (1R)-1-([[(1R,2R)-1-([[(1S)-2-[[(1R,13S,16S,17R,28R)-20-chloro-17,25-dihydroxy-5,8,10,24-tetramethoxy-13-[[(2-methoxyethoxy)methoxy]methyl]-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.2(18,21).1(2,6).1(23,27).0(7,12)]hexatriac | C66H77ClFN9O21 | 详情 | 详情 | |
| (XIII) | 42053 | tert-butyl (1R)-1-([[(1S,2R,18R,19R,22S,25R,28R,40S)-5-chloro-22-(cyanomethyl)-2,18-dihydroxy-32,35,37,50-tetramethoxy-40-[[(2-methoxyethoxy)methoxy]methyl]-15-nitro-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6). | C66H76ClN9O21 | 详情 | 详情 | |
| (XIV) | 42054 | tert-butyl (1R)-1-([[(1S,2R,18R,19R,22S,25R,28R,40S)-15-amino-5-chloro-22-(cyanomethyl)-2,18-dihydroxy-32,35,37,50-tetramethoxy-40-[[(2-methoxyethoxy)methoxy]methyl]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6). | C66H78ClN9O19 | 详情 | 详情 | |
| (XV) | 42055 | tert-butyl (1R)-1-([[(1S,2R,18R,19R,22S,25R,28R,40S)-5,15-dichloro-22-(cyanomethyl)-2,18-dihydroxy-32,35,37,50-tetramethoxy-40-[[(2-methoxyethoxy)methoxy]methyl]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14 | C66H76Cl2N8O19 | 详情 | 详情 | |
| (XVI) | 42056 | tert-butyl (1R)-1-([[(1S,2R,18R,19R,22S,25R,28R,40S)-2,18-bis[[tert-butyl(dimethyl)silyl]oxy]-5,15-dichloro-22-(cyanomethyl)-32,35,37,50-tetramethoxy-40-[[(2-methoxyethoxy)methoxy]methyl]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoct | C78H104Cl2N8O19Si2 | 详情 | 详情 |